Erymildbraedin A and B, two novel cytotoxic dimethylpyrano-isoflavones from the stem bark of Erythrina mildbraedii: evaluation of their activity toward endocrine cancer cells

References

• Mitscher AL, Drake S, Gollapudi SR, Simon K, Okwute SR. A modern look at folkloric use of anti-infective agents. J Nat Prod 1987;50:1025–40.
   PubMed Web of Science ®Google Scholar
• Burkill HM. The Useful Plants of West Tropical Africa, Vol. 3, Families J–L. Kew: Royal Botanic Gardens, 1995.
   Google Scholar
• Tsuda Y, Sano T. Erythrina,and related alkaloids. In: Cordell AG, ed., The alkaloids: chemistry and biology. Vol.48. San Diego: Academic Press, 1996:249–337.
   Google Scholar
• Heywood VH. Les Plantes à Fleurs, 306 Familles de la Flore Mondiale. Paris: Nathan, 1996:149–52.
   Google Scholar
• Amer ME, Shamma M, Freyer AJ. The tetracyclic Erythrina alkaloids. J Nat Prod 1991;54:329–63.
   Web of Science ®Google Scholar
• Mitscher AL, Okwute SK, Gollapudi SR, Drake S, Avona E. Antimicrobial pterocarpans of Nigerian Erythrina mildbraedii. Phytochemistry 1988;27:3449–52.
   Web of Science ®Google Scholar
• Njamen D, Talla E, Mbafor JT, Fomum ZT, Kamanyi A, Mbanya JC, et al. Anti-inflammatory activity of erycristagallin a pterocarpene from Erythrina mildbraedii. Eur J Pharmacol 2003;468:67–74.
   PubMed Web of Science ®Google Scholar
• Jang J, Na M, Thuong PT, Njamen D, Mbafor JT, Fomum ZT, et al. Prenylated flavonoids with PTP1B inhibitory activity from the root bark of Erythrina mildbraedii. Chem Pharm Bull 2008;56:85–8.
   PubMed Web of Science ®Google Scholar
• Shi YQ, Fukai T, Sakagami H, Chang WJ, Yang P, Wang FP, et al. Cytotoxic flavonoids with isoprenoid groups from Morus mongolica. J Nat Prod 2001;64:181–8.
   PubMed Web of Science ®Google Scholar
• Katsanou ES, Halabalaki M, Aligiannis N, Mitakou S, Skaltsounis AL, Alexi X, et al. Cytotoxic effects of 2-arylbenzofuran phytoertrogen on human cancer cells: modulation by adrenal and gonadal steroids. J Steroid Biochem Mol Biol 2007;104:228–36.
   Google Scholar
• Halabalaki M, Alexi X, Aligiannis N, Alexis MN, Skaltsounis AL. Ebenfurans IV-VIII from Onobrychis ebenoides: evidence that C-prenylation is the key determinant of the cytotoxicity of 3-formyl-2-arylbenfurans. J Nat Prod 2008;71:1934–7.
   PubMed Web of Science ®Google Scholar
• Fokialakis N, Lambrinidis G, Mitsiou DJ, Aligiannis N, Mitakou S, Skaltsounis AL, et al. A new class of phytoestrogens: evaluation of the estrogenic activity of deoxybenzoins. Chem Biol 2004;11:397–406.
   PubMedGoogle Scholar
• Halabalaki M, Alexi X, Aligiannis N, Lambrinidis G, Pratsinis H, Florentin I, et al. Estrogenic activity of isoflavonoids from Onobrychis ebenoides. Planta Med 2006;72:488–93.
   PubMed Web of Science ®Google Scholar
• Tsukamoto H, Hisada S, Nishibe S. Coumarins from bark of Fraxinus japonica and F. mandshurica var. japonica. Chem Pharm Bull 1985;33:4069–73.
   Web of Science ®Google Scholar
• Van Puyvelde L, De Kimpe N, Ayobangira F, Costa J, Nshimyumukiza P, Boily Y, et al. Wheat rootlet growth inhibition test of Rwandese medicinal plants: active principles of Tetradenia riparia and Diplolophium Africanum. J Ethnopharmacol 1988;24:233–46.
   PubMed Web of Science ®Google Scholar
• Fomum ZT, Ayafor JF, Wandji J. Erythrisenegalone, a prenylated-flavanone from Erythrina senegalensis. Phytochemistry 1985;24: 3075–6.
   Web of Science ®Google Scholar
• Wandji J, Awanchiri SS, Fomum ZT, Tillequin F, Libot F. Isoflavones and alkaloids from the stem bark and seeds of Erythrina senegalensis. Phytochemistry 1995;39:677–81.
   Web of Science ®Google Scholar
• Xiaoli L, Naili W, Wongman S, Albert CSC, XIinsheng Y. Four new isoflavones from stem bark of Erythrina variegata. Chem Pharm Bull 2006;54:570–3.
   PubMed Web of Science ®Google Scholar
• Tanaka H, Etoh H, Shimizu H, Makita T, Tateishi Y. Two isoflavonoids from Erythrina variegata. Planta Med 2000;66:578–9.
   PubMed Web of Science ®Google Scholar
• Gantimur D, Semenov AA. Coumarins from Phlojodicarpus sibiricus. Chem Nat Compd 1981;17:41–3.
   Google Scholar
• Laguna A, Fajardo M. Phytochemical study of the aerial parts of Amyris stromatophylla. Rev CENIC Cienc Quim 1999;30:95–7.
   Google Scholar
• Prawat H, Mahidol C, Ruchirawat S. Reinvestigation of Derris reticulate. Pharm Biol 2000;38(Suppl.):63–7.
   PubMed Web of Science ®Google Scholar
• Ito C, Itoigawa M, Mishina Y, Cechinel Filho V, Mukainaka T, Tokuda H, et al. Chemical constituents of Calophyllum brasiliensis: structure elucidation of seven new xanthones and their cancer chemopreventive activity. J Nat Prod 2002;65:267–72.
   PubMed Web of Science ®Google Scholar
• Migliaccio A, Castoria G, Di Domenico M, de Falco A, Bilancio A, Lombardi M, et al. Steroid-induced androgen receptor-oestradiol receptor β-Src complex triggers prostate cancer cell proliferation. EMBO J 2000;19:5406–17.
   PubMed Web of Science ®Google Scholar
• Wittmann BM, Sherk A, McDonnell DP. Definition of functionally important mechanistic differences among selective estrogen down-regulators. Cancer Res 2007;67:9549–60.
   PubMed Web of Science ®Google Scholar
• Maggiolini M, Vivacqua A, Carpino A, Bonofiglio D, Fasanella G, et al. The mutant androgen receptor T877A mediates the proliferative but not the cytotoxic dose-dependent effects of genistein and quercetin on human LNCaP prostate cancer cells. Mol Pharmacol 2002;62:1027–35.
   PubMed Web of Science ®Google Scholar
• Gardner CD, Chatterjee LM, Franke AA. Effects of isoflavone supplements vs. soy foods on blood concentrations of genistein and daidzeinin adults. J Nutr Biochem 2009;20:227–34.
   PubMed Web of Science ®Google Scholar
• Nettles KW, Bruning JB, Gil G, O’Neill EE, Nowak J, Guo Y, et al. Structural plasticity in the oestrogen receptor ligand-binding domain. EMBO Rep 2007;8:563–8.
   PubMed Web of Science ®Google Scholar
• Daskiewicz JB, Depeint F, Viornery L, Bayet C, Comte-Sarrazin G, Comte G, et al. Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study. J Med Chem 2005;48:2790–804.
   PubMed Web of Science ®Google Scholar
• Pan L, Becker H, Gerhäuser C. Xanthohumol induces apoptosis in cultured 40-16 human colon cancer cells by activation of the death receptor- and mitochondrial pathway. Mol Nutr Food Res 2005;49:837–43.
   PubMed Web of Science ®Google Scholar
• Ito C, Murata T, Itoigawa M, Nakao K, Kumagai M, Kaneda N, et al. Induction of apoptosis by isoflavonoids from the leaves of Milletia taiwaniana in human leukemia HL-60 cells. Planta Med 2006; 72:424–9.
   PubMed Web of Science ®Google Scholar
• Nkengfack AE, Azebaze AG, Waffo AK, Fomum ZT, Meyer M, Van Heerden FR. Cytotoxic isoflavones from Erythrina indica. Phytochemistry 2001;58:1113–20.
   PubMed Web of Science ®Google Scholar
• Wang BH, Ternai B, Polya G. Specific inhibition of cyclic AMP-dependent protein kinase by warangalone and robustic acid. Phytochemistry 1997;44:787–96.
   PubMed Web of Science ®Google Scholar
• Oh WK, Kim BY, Oh H, Kim BS, Ahn JS. Phospholipase Cγ1 inhibitory activities of prenylated flavonoids isolated from Erythrina senegalensis. Planta Med 2005;71:780–1.
   PubMed Web of Science ®Google Scholar
• Cui L, Thuong PT, Lee HS, Ndinteh DT, Mbafor JT, Fomum ZT, et al. Flavanones from the stem bark of Erythrina abyssinica. Bioorg Med Chem 2008;16:10356–62.
   PubMed Web of Science ®Google Scholar
• Balsamo J, Arregui C, Leung T, Lilien J. The nonreceptor protein tyrosine phosphatase PTP1B binds to the cytoplasmic domain of N-cadherin and regulates the cadherin-actin linkage. J Cell Biol 1998;143:523–32.
   PubMed Web of Science ®Google Scholar